Conditions | Yield |
---|---|
With chloroform In toluene under Ar; stirred at 20°C for 5 h; stored overnight at 0-5°C; evaporated, extracted (THF); elem. anal.; | A 57% B 88% |
1,2-Dichloroethylene
A
dichloromethane
B
1,2-bis(trichlorosilyl)ethane
C
1,2-bis(trichlorosilyl)ethene
D
1,1,1,3,3,3-hexachloro-1,3-disilapropane
Conditions | Yield |
---|---|
With hexachlorodisilane at 550℃; for 0.00833333h; | A n/a B n/a C 83% D n/a |
Conditions | Yield |
---|---|
With KOH In water; butan-1-ol heating of (CH3)2(CHCl2)SiOSi(CH3)2(CHCl2) and 10% KOH in n-butanol/H2O at 45°C under reduced pressure;; | 78% |
With KOH In potassium hydroxide aq. KOH; (CH3)2(CHCl2)SiOSi(CH3)2(CHCl2) and 40% aq. KOH;; | |
With potassium hydroxide In potassium hydroxide (CH3)2(CHCl2)SiOSi(CH3)2(CHCl2) and 40% aq. KOH;; |
Conditions | Yield |
---|---|
With chloroform In toluene under Ar; excess of CHCl3 added to suspension of Cp3ZrH in PhMe; stirred at about 20°C for 5 h; stored overnight at 0-5°C; evaporated, extracted (THF), filtered; filtrate evapd.; elem. anal.; | A 70% B 42% |
Conditions | Yield |
---|---|
With sulfur dioxide; chlorine at 25℃; under 2250.23 Torr; for 1h; Concentration; Wavelength; Irradiation; | A n/a B 69% |
Conditions | Yield |
---|---|
With chloroform In toluene under Ar; elem. anal.; | A 67% B 43% |
methane
A
tetrachloromethane
B
methylene chloride
C
dichloromethane
D
chloroform
E
methanesulfonyl chloride
Conditions | Yield |
---|---|
With hydrogenchloride; sulfur dioxide; chlorine at 63 - 67℃; under 6750.68 Torr; Photolysis; | A n/a B n/a C n/a D n/a E 55% |
methane
A
dichloromethane
B
chloroform
C
methanesulfonyl chloride
Conditions | Yield |
---|---|
With sulfur dioxide; chlorine at 65℃; under 2250.23 Torr; for 1h; Temperature; Irradiation; | A n/a B n/a C 54.9% |
Conditions | Yield |
---|---|
With tetra-n-butylphosphonium formate In water at -20 - 22℃; for 1.33333h; Reagent/catalyst; | A 26% B 52% |
With [RuCl(1-butyl-3-methyl-imidazole)(1,3,5-triaza-7-phosphatricyclo[3.3.1.1]3,7decane)(η6-p-cymene)]Cl; hydrogen; sodium formate In water at 80℃; under 7500.75 Torr; for 2h; Schlenk technique; Sealed tube; | A 12.9% B 29% |
With isopropyl alcohol; dimanganese decacarbonyl at 120℃; Product distribution; catalyst and temperature effects; |
Conditions | Yield |
---|---|
With iodine trichloride Product distribution; further iodoalkanes; | A 34% B 50% |
Dichlorofluoromethane
benzene-d6
Triethylgerman
A
R32
B
dichloromethane
C
bis-pentadeuteriophenyl-methane
D
triethylchlorogermane
Conditions | Yield |
---|---|
With ACF. Et3GeH In benzene-d6 at 70℃; for 216h; Schlenk technique; Inert atmosphere; | A 50% B 11% C 39% D n/a |
chloro-trimethyl-silane
chloroform
A
dichloromethane
B
trichloromethyltrimethylsilane
Conditions | Yield |
---|---|
With hexaethylphosphoric triamide In acetonitrile at 20℃; for 144h; | A n/a B 47% |
chloroform
A
dichloromethane
B
(dichlorosilylmethyl)trichlorosilane
C
1,1,1,3,3,3-hexachloro-1,3-disilapropane
Conditions | Yield |
---|---|
With trichlorosilane at 100℃; for 8h; | A 42% B 5% C 42% |
Chlorodifluoromethane
Triethylgerman
A
methylene chloride
B
dichloromethane
C
trifluoromethan
D
triethylchlorogermane
Conditions | Yield |
---|---|
With ACF. Et3GeH at 25℃; for 72h; Schlenk technique; Inert atmosphere; | A 41% B 32% C 27% D n/a |
chloroform
aniline
A
dichloromethane
B
phenyl isocyanate
C
Azobenzene
D
N-phenylphenylene-1,4-diamine
E
N-phenyl-1,2-benzenediamine
F
1,1,2,2-tetrachloroethane
Conditions | Yield |
---|---|
at 15℃; for 24h; Product distribution; Mechanism; Irradiation; | A n/a B 30.2% C 12.5% D 10.5% E 18.4% F n/a |
chloroform
Triethylgerman
A
methylene chloride
B
dichloromethane
C
triethylchlorogermane
Conditions | Yield |
---|---|
With ACF. Et3GeH at 70℃; Schlenk technique; Glovebox; | A 22% B n/a C n/a |
Dichlorofluoromethane
Triethylgerman
A
Difluoromethane
B
dichloromethane
C
trifluoromethan
D
Chlorodifluoromethane
E
triethylchlorogermane
Conditions | Yield |
---|---|
With ACF. Et3GeH at 25℃; for 72h; Schlenk technique; Inert atmosphere; | A n/a B n/a C 22% D 16% E n/a |
methylenesulfurtetrafluoride
A
dichloromethane
B
Methylschwefelpentafluorid
C
cis-Methylschwefelchloridtetrafluorid
D
cis-(Chlormethyl)schwefelchloridtetrafluorid
Conditions | Yield |
---|---|
With chlorine In trichlorofluoromethane at -78℃; | A n/a B n/a C n/a D 20% E n/a |
chloroform
benzene-d6
Triethylgerman
A
dichloromethane
B
bis-pentadeuteriophenyl-methane
C
triethylchlorogermane
Conditions | Yield |
---|---|
With ACF. Et3GeH at 70℃; Schlenk technique; Glovebox; | A n/a B 18% C n/a |
methane
A
tetrachloromethane
B
methylene chloride
C
dichloromethane
D
chloroform
Conditions | Yield |
---|---|
With chlorine for 4h; Product distribution; Ambient temperature; var. catalysts and times; | A 4.8% B 6.5% C 15% D 14% |
With molybdenum(V) chloride at 699.9℃; Product distribution; Mechanism; var. time, temp., and transition-metal chlorides; var. methane and argon flow rates; | |
With copper dichloride In melt at 449.9℃; Kinetics; Product distribution; further temperatures and concentrations; |
tetrachloromethane
Triethylgerman
A
dichloromethane
B
chloroform
C
triethylchlorogermane
Conditions | Yield |
---|---|
With ACF. Et3GeH at 70℃; Schlenk technique; Glovebox; | A 8% B n/a C n/a |
tetrachloromethane
benzene-d6
Triethylgerman
A
dichloromethane
B
chloroform
C
bis-pentadeuteriophenyl-methane
D
triethylchlorogermane
Conditions | Yield |
---|---|
With ACF. Et3GeH at 70℃; Schlenk technique; Glovebox; | A 7% B n/a C 6% D n/a |
pentacarbonyl(methoxyphenylmethylene)tungsten(0)
A
1,1,2,2-tetrachloroethylene
B
methylene chloride
C
dichloromethane
D
chloroform
Conditions | Yield |
---|---|
In tetrachloromethane byproducts: HCl, Cl2; further products; N2; stirred; gas-chromy., MAS; elem. anal.; | A 6.8% B 2% C 0.2% D 3.6% |
Conditions | Yield |
---|---|
With isopropyl alcohol In acetonitrile at 20℃; Reagent/catalyst; | |
With sodium hydroxide; iron(II) sulfate |
Conditions | Yield |
---|---|
With potassium hydroxide; tetrabutylammomium bromide for 13h; Ambient temperature; | 100% |
With sodium hydroxide; phase transfer catalysis by tetraethylammonium bromide for 16h; Ambient temperature; | 96% |
With tetrabutylammomium bromide; sodium hydroxide Inert atmosphere; Reflux; | 87% |
acetophenone oxime
dichloromethane
1-Phenyl-ethanone O-[1-phenyl-eth-(E)-ylideneaminooxymethyl]-oxime
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate | 100% |
With 1-butyl-3-methylimidazolium Tetrafluoroborate; sodium hydroxide at 20℃; for 0.5h; | 96% |
With sodium hydroxide In water for 17.5h; | 95% |
With sodium hydroxide; trialkyl-methyl-ammonium chloride |
3-benzoylpyrrole
dichloromethane
[1-(2-Benzoyl-pyrrol-1-ylmethyl)-1H-pyrrol-2-yl]-phenyl-methanone
Conditions | Yield |
---|---|
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In dichloromethane for 4h; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide; benzyltrimethylammonium chloride In water at 40℃; for 72h; | 100% |
With potassium hydroxide; benzyltrimethylammonium chloride In dichloromethane at 40℃; for 72h; | 100% |
Stage #1: 4-chloro-phenol With sodium hydride In 1-methyl-pyrrolidin-2-one Stage #2: dichloromethane In 1-methyl-pyrrolidin-2-one at 40℃; for 9h; | 98% |
With 1-methyl-pyrrolidin-2-one; sodium hydride at 40℃; for 9h; | 98% |
With sodium hydroxide; Amberlite IRA-400 (Cl-) 2.) reflux, 15 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With potassium hydroxide; octopus-type calixarene at 40℃; for 24h; Product distribution; also with substituted phenols; effect of catalysts poly(ethylene glycol)diethyl ether, poly(ethylene glycol), benzyltrimethylammonium chloride, none; also with water solvent; | 100% |
With potassium hydroxide; octopus-type calixarene at 40℃; for 24h; | 100% |
With potassium hydroxide; 5,11,17,23,29,35-Hexa-p-tert-butyl-37,38,39,40,41,42-hexakis-(3,6,9-trioxadecyloxy)calix<6>arene In dichloromethane at 40℃; for 24h; | 100% |
dichloromethane
(2R,3R)-3-(methylamino)-3-phenyl-1,2-propanediol
Conditions | Yield |
---|---|
at 100℃; for 28h; Cyclization; | 100% |
Conditions | Yield |
---|---|
at 55℃; | 100% |
dichloromethane
diethylamine
2,2-dimethyl-2H-1-benzopyran-6-sulfonyl chloride
N,N-diethyl-2,2-dimethyl-2H-1-benzopyran-6-sulfonamide
Conditions | Yield |
---|---|
In water | 100% |
dichloromethane
1-(bromomethyl)-4-methyl-2-(phenylmethoxy)benzene
<4-methyl-2-(phenylmethoxy)phenyl>acetonitrile
Conditions | Yield |
---|---|
With NaCN; tetrabutylammomium bromide In water | 100% |
dichloromethane
2-fluorobenzonitrile
(2S)-2-amino-5-(2-cyanophenylamino)pentanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; acetic acid In ethanol; water | 100% |
dichloromethane
5-Chlorovaleroyl chloride
1,4-dihydro-4-(3-aminophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid,dimethyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran; water; ethyl acetate | 100% |
In tetrahydrofuran; water; ethyl acetate | 100% |
In tetrahydrofuran; water; ethyl acetate | 100% |
dichloromethane
2-bromo-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid phenylmethyl ester
2-bromo-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide
Conditions | Yield |
---|---|
With hydrogenchloride; aluminium In benzene | 100% |
2-carboxy-4-chloroquinoline
dichloromethane
water
Methyl-4-chloroquinaldate
Conditions | Yield |
---|---|
With NaH In N,N-dimethyl-formamide | 100% |
dichloromethane
tert-butylamine
3,4-diethoxy-3-cyclobuten-1,2-dione
3-(1,1-dimethylethylamino)-4-ethoxy-3-cyclobutene-1,2-dione
Conditions | Yield |
---|---|
In tetrahydrofuran; methanol | 100% |
dichloromethane
di-tert-butyl dicarbonate
Conditions | Yield |
---|---|
100% |
5-METHOXY-2-((3,5-DIMETHYL-4-NITRO-2-PYRIDINYL-N-OXIDE)-METHYLTHIO)-1H-BENZIMIDAZOLE
dichloromethane
5-methoxy-2-[[(4-methoxy-3,5-dimethylpyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzimidazole
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; sodium methylate In methanol; water | 100% |
diazomethane
methyl α-tert-butoxycarbonylamino-p-carboxymethylphenylacetate
dichloromethane
Methyl α-tert-butoxycarbonylamino-p-methoxycarbonylmethylphenylacetate
Conditions | Yield |
---|---|
100% |
Conditions | Yield |
---|---|
In ethanol (under Ar, Schlenk); Rh-complex added to refluxing soln. of Sb(C6H5)3 inEtOH; ppt. filtered, washed with CH2Cl2/hexane, dried in vacuo; elem. anal.; | 100% |
Conditions | Yield |
---|---|
In acetone byproducts: AgCl; soln. of palladium complex treated with AgClO4 in absence of light; 30 min stirred at room temp.; added to soln. of p-nitroaniline; soln. stirred at room temp. for 30 min; solvent evapd.; oil treated with Et2O; solid pptd.; elem. anal.; | 100% |
dichloromethane
Conditions | Yield |
---|---|
In dichloromethane soln. of Pt complex in CH2Cl2 stored at room temp. for 10 d; solvent evapd.; washed with hexane; elem. anal.; | 100% |
Conditions | Yield |
---|---|
In not given Atherton, M. J.; Fawcett, J.; Holloway, J. H.; Hope, E. G.; Karacar, A.;Russell, D. R.; Saunders, G. C. J. Chem. Soc., Dalton Trans. 1996, 321 5; elem. anal.; | 100% |
dichloro( 1,5-cyclooctadiene)platinum(ll)
dichloromethane
(bromodifluoromethyl)diphenylphosphine
Conditions | Yield |
---|---|
In dichloromethane by a react. of Ph2PCF2Br with Pt-contg. compd. at 20°C for 0.2 h; elem. anal.; | 100% |
tetrakis(actonitrile)copper(I) hexafluorophosphate
dichloromethane
n-butyl isonitrile
3,5-bis[bis-(4,5-diphenyl-1-methylimidazol-2-yl)methoxymethyl]pyrazole
Conditions | Yield |
---|---|
With KOC(CH3)3 In tetrahydrofuran; acetonitrile (N2, glove box) a soln. of Cu-complex in CH3CN was added to a soln. of pyrazole-compound and KOC(CH3)3 in THF, stirred for 15 min, n-butylisocyanide was added, stirred for 20 min; the solvent was removed in vac., the solid was dissolved in CH2Cl2 and filtered; elem. anal.; | 100% |
trichlorotris(tetrahydrofuran)chromium(III)
dichloromethane
2,6-bis(1-methylimidazol-2-ylidene)pyridine
Conditions | Yield |
---|---|
In tetrahydrofuran (N2); std. Schlenk technique; soln. of carbene in THF was slowly added to soln. of Cr complex in THF; stirred for 1 h; filtered; washed (THF, CH2Cl2); dried (vac.); elem. anal.; | 100% |
Conditions | Yield |
---|---|
at 25℃; Kinetics; | 100% |
Conditions | Yield |
---|---|
In dichloromethane (N2, Schlenk) a soln. of complex in CH2Cl2 allowed to stand for 2 h; volatiles were removed under vac.; elem. anal.; | 100% |
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
dichloromethane
Conditions | Yield |
---|---|
In dichloromethane (under N2, Schlenk); soln. of Ru-complex in CH2Cl2 added dropwise to soln. of ligand in CH2Cl2, stirred for 1 h; concd., hexane added; elem. anal.; | 100% |
Conditions | Yield |
---|---|
In chloroform at 60℃; under 14251400 Torr; for 24h; Kinetics; Pressure; Temperature; Menshutkin Reaction; High pressure; Autoclave; | 100% |
for 0.25h; Microwave irradiation; Reflux; | 48% |
at 75℃; for 24h; | 42.6% |
Conditions | Yield |
---|---|
With [D]-sodium hydroxide; sodium acetate In water-d2 for 2h; pD >11; | 100% |
Conditions | Yield |
---|---|
In acetonitrile inert atmosphere, Schlenk technique; soln. of Pd-complex in CH3CN treated at -40 °C with (H3C)3OBF4, stirred at -40 °C for 60 min,warmed to room temp., solvent removed (vac.), recrystd. from petroleum ether/CH2Cl2; elem. anal.; | 100% |
Basic Information of Dichloromethane:
Dichloromethane (CAS NO.75-09-2) is a colorless liquid with a sweet, penetrating-like ether. If exposed to high temperatures , it may emit toxic chloride fumes. Vapors are narcotic in high concentrations. Used as a solvent and paint remover. It is somewhat soluble in water, subjected to slow hydrolysis which is accelerated by light. It has some kinds of uses. Solvent is the most important use of methylene chloride. Dichloromethane with the dissolving ability, low boiling point and relatively low toxicity, so it has be made as the highest frequency use in organic synthesis. It can be used as extraction solvent, mainly as the extraction of caffeine in coffee beans, besides it can be used as hops, spices oil-resin extraction solvents, pigment thinner, organic synthesis. As a solvent for resins and plastics industry is widely used in pharmaceutical, plastics and film industries.
Physical properties about Dichloromethane are:
(1)ACD/LogP: 1.405; (2)ACD/LogD (pH 5.5): 1.41; (3)ACD/LogD (pH 7.4): 1.41; (4)ACD/BCF (pH 5.5): 6.88; (5)ACD/BCF (pH 7.4): 6.88; (6)ACD/KOC (pH 5.5): 138.38; (7)ACD/KOC (pH 7.4): 138.38; (8)Index of Refraction: 1.398; (9)Molar Refractivity: 16.38 cm3; (10)Molar Volume: 67.812 cm3; (11)Polarizability: 6.494 10-24cm3; (12)Surface Tension: 23.1989994049072 dyne/cm; (13)Density: 1.252 g/cm3; (14)Flash Point: -14.127 °C; (15)Enthalpy of Vaporization: 28.06 kJ/mol; (16)Boiling Point: 39.639 °C at 760 mmHg; (17)Vapour Pressure: 448.006011962891 mmHg at 25°C
Preparation of Dichloromethane:
Dichloromethane is produced by treating either methyl chloride or methane with chlorine gas at 400–500 °C. At these temperatures, both methane and methyl chloride undergo a series of reactions producing progressively more chlorinated products.
CH4 + Cl2 → CH3Cl + HCl
CH3Cl + Cl2 → CH2Cl2 + HCl
CH2Cl2 + Cl2 → CHCl3 + HCl
CHCl3 + Cl2 → CCl4 + HCl
The output of these processes is a mixture of methyl chloride, dichloromethane, chloroform, and carbon tetrachloride. These compounds are separated by distillation.
Uses of Dichloromethane:
DCM's volatility and ability to dissolve a wide range of organic compounds makes it a useful solvent for many chemical processes. Concerns about its health effects have led to a search for alternatives in many of these applications. It is widely used as a paint stripper and a degreaser. In the food industry, it has been used to decaffeinate coffee and tea as well as to prepare extracts of hops and other flavorings.[2] Its volatility has led to its use as an aerosol spray propellant and as a blowing agent for polyurethane foams.
You can still convert the following datas into molecular structure:
(1)InChI=1S/CH2Cl2/c2-1-3/h1H2;
(2)InChIKey=YMWUJEATGCHHMB-UHFFFAOYSA-N;
(3)Smiles=C(Cl)Cl;
The toxicity data of Dichloromethane is as follows:
Organism Test Type Route Reported Dose (Normalized Dose) Effect Source man TDLo oral 1329ug/kg/31D (1.329mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED American Journal of Gastroenterology. Vol. 83, Pg. 576, 1988.
man TDLo oral 21mg/kg/26W-I (21mg/kg) PERIPHERAL NERVE AND SENSATION: FASCICULATIONS Postgraduate Medical Journal. Vol. 63, Pg. 311, 1987. mouse LD50 intraperitoneal 13300mg/kg (13300mg/kg) Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 811, 1980. mouse LD50 intravenous > 18mg/kg (18mg/kg) Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 811, 1980. mouse LD50 oral 2gm/kg (2000mg/kg) Polish Journal of Pharmacology and Pharmacy. Vol. 35, Pg. 77, 1983. mouse LD50 subcutaneous > 10gm/kg (10000mg/kg) Drugs in Japan Vol. 6, Pg. 235, 1982. rat LD50 intraperitoneal 14200mg/kg (14200mg/kg) Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 811, 1980. rat LD50 oral > 15gm/kg (15000mg/kg) Drugs in Japan Vol. 6, Pg. 235, 1982. rat LD50 subcutaneous > 10gm/kg (10000mg/kg) Drugs in Japan Vol. 6, Pg. 235, 1982.
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